A 42mm 8500 PO is very.....very well made and worth every cent of it's asking price. If you do not mind preowned, it can be quite a bargain and within your budget. The finishing is top notch.
But being a 14060M owner, I might be just a tad bias to say that I would still chose the Sub over the PO. I just prefer how it looks and feel on my wrist. All is individual I would reckon. The PO sits a bit higher due to the sapphire case back. But I must admit the finishing of the movement, dial, case and etc..is beautiful for it's price range.
Since these 2 models are quite a norm in both preowned shops and ADs, I would recommend make a visit to try 'em on your wrist. Your heart would tell you the answer.
Don't worry about resale prices. I find it funny that guys fret so much about resale prices when they would definitely be way poorer if they get divorced. If that matters so much, then don't get married and buy selected Rolex sports model only.